UWA-001

UWA-001
Identifiers
	IUPAC name 2-(1,3-benzodioxol-5-yl)-N-methyl-1-phenylethanamine;
CAS Number	1350821-28-1;
PubChemCID	17757315;
ChemSpider	34245583;
UNII	ZQ2R4KPZ2W;
ChEMBL	ChEMBL3303514;
CompTox Dashboard(EPA)	DTXSID301045824;
Chemical and physical data
Formula	C16H17NO2
Molar mass	255.317g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNC(Cc1ccc2OCOc2c1)c3ccccc3;
	InChI InChI=1S/C16H17NO2/c1-17-14(13-5-3-2-4-6-13)9-12-7-8-15-16(10-12)19-11-18-15/h2-8,10,14,17H,9,11H2,1H3; Key:DNOTUUOUOFJQJC-UHFFFAOYSA-N;

UWA-001(also known asα-phenyl-MDMAandmethylenedioxymephenidine) is aphenethylaminederivative invented at theUniversity of Western Australiaas non-toxic alternative to3,4-methylenedioxy-N-methylamphetamine(MDMA) and researched as a potential treatment forParkinson's disease.^[1]

It has a5-HT_2Areceptoraffinity of 1.2 μM (~10-fold increase compared to MDMA), 1.3 μM for theserotonin transporter(~4-fold decrease compared to MDMA), 13.4 μM for thenorepinephrine transporter(~26-fold increase compared to MDMA) and virtually no affinity for thedopamine transporter(>50 μM).^[1]

Unlike MDMA andpara-methoxyamphetamine(but similarly toketamine),^[2]UWA-001 increasesprepulse inhibitionand was therefore considered to be non-psychoactive, though it was not assayed at other binding sites.^[3]It is toxic to theSH-SY5Ycell line at high concentrations, however significantly less toxic than MDMA at all concentrations tested.^[3]

UWA-001 is structurally related to the diarylethylamineslefetamine(astimulantandopioid) and thedissociative anesthetic ephenidine,which acts as aNMDA receptor antagonist.

References[edit]

^^a ^bJohnston TH, Millar Z, Huot P, Wagg K, Thiele S, Salomonczyk D, et al. (May 2012)."A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances L-DOPA benefit in parkinsonian primates".FASEB Journal.26(5): 2154–63.doi:10.1096/fj.11-195016.PMID 22345403.S2CID 37589231.
^Abel KM, Allin MP, Hemsley DR, Geyer MA (May 2003). "Low dose ketamine increases prepulse inhibition in healthy men".Neuropharmacology.44(6): 729–37.doi:10.1016/S0028-3908(03)00073-X.PMID 12681371.S2CID 25706718.
^^a ^bGandy MN, McIldowie M, Lewis K, Wasik AM, Salomonczyk D, Wagg K, et al. (2010). "Redesigning the designer drug ecstasy: non-psychoactive MDMA analogues exhibiting Burkitt's lymphoma cytotoxicity".MedChemComm.1(4): 287–93.doi:10.1039/C0MD00108B.

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[Johnston-1] Johnston TH, Millar Z, Huot P, Wagg K, Thiele S, Salomonczyk D, et al. (May 2012)."A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances L-DOPA benefit in parkinsonian primates".FASEB Journal.26(5): 2154–63.doi:10.1096/fj.11-195016.PMID 22345403.S2CID 37589231.

[2] Abel KM, Allin MP, Hemsley DR, Geyer MA (May 2003). "Low dose ketamine increases prepulse inhibition in healthy men".Neuropharmacology.44(6): 729–37.doi:10.1016/S0028-3908(03)00073-X.PMID 12681371.S2CID 25706718.

[Gandy-3] Gandy MN, McIldowie M, Lewis K, Wasik AM, Salomonczyk D, Wagg K, et al. (2010). "Redesigning the designer drug ecstasy: non-psychoactive MDMA analogues exhibiting Burkitt's lymphoma cytotoxicity".MedChemComm.1(4): 287–93.doi:10.1039/C0MD00108B.

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v t e Phenethylamines
Phenethylamines	Psychedelics:25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants:Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine(amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens:Lophophine MDPEA MDMPEA Others:BOH DMPEA
Amphetamines	Psychedelics:3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants:2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine(Dextroamphetamine,Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine(Dexfenfluramine,Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine(Dextromethamphetamine,Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens:4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others:3,4-DCA Amiflamine DiFMDA Selegiline(alsoD-Deprenyl)
Phentermines	Stimulants:Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens:MDPH MDMPH Others:Cericlamine
Cathinones	Stimulants:3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens:3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens:4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants:Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants:α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA(Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA(Levodopa) L-DOPS(Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin(Levonordefrin) Norepinephrine Norfenefrine(m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol(Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

See also[edit]

References[edit]